A pirates lair, a leper colony, and a penitentiary for political prisoners — much like Koh Tao in Thailand and Isla de Coiba in Panama, Ilha Grande in Brazil has quite the illicit past. And much like those islands before it, this one also managed to steal my heart in just a few short days.

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Though the last island prison dissolved in the mid-90’s, gorgeous Ilha Grande’s sordid reputation kept developers at bay, much to the delight of travelers now lucky enough to stumble upon it. And it’s pretty convenient to stumble onto — several boat and van services offer door-to-door connections between Paraty and Rio, making Ilha Grande a natural stop on a hop along Brazil’s emerald coastline.

The first stop for visitors to the island is Vila Do Abraão, a once sleepy fishing village now bursting with pousadas, canga shops, açaí stands and other tourist trappings that manage to maintain the tiny town’s ramshackle charm. Adding to the adorability factor is the lack of motorized vehicles. A garbage truck, a fire truck and a police vehicle make up the list of exceptions, and everyone else gets around on foot or by bicycle.

After our rainy five days in Paraty, we could not have been any more thrilled to be greeted by the sun in Ilha Grande. Yet we quickly learned that one thing we were seriously unprepared for pretty much all through Brazil, with the exception of our first lucky week? The weather.

We spent three glorious nights on Ilha Grande, and during the day the weather was beautiful and the temperatures in the high sixties to low eighties. But with strong island winds and temperatures dropping into the fifties at night, we were seriously unprepared for anything Brazil was throwing at us past sunset — which was around 5:30pm at that time of year.

Thank goodness I had bought a pair of jeans specifically for this trip! We fell into a pattern of enthusiastically planning a night out every day, then gradually putting on every layer we had in our bags as the temperature dropped until we were huddled in our beds wrapped in our comforters cursing ourselves for having acclimated so seamlessly to the tropical climates of our adopted homes. The last thing I expected to be on this Brazilian holiday was cold — though on the upside, I’ve lived happily through a Thai heat wave with no air conditioning, so there’s that!

We’d waffled on where to stay in Ilha Grande, entertaining lush pousadas, budget hostels and even a charming houseboat on Airbnb. In the end, we settled on the Che Legarto Paraty, a sister property to the hostel we’d tried in Paraty.

We’d been won over by the waterfront location, though I can’t say I’m itching to return. Our dorms were pricey at $25 per night per person (private rooms are no longer offered), the included breakfast was pitiful, the location was a bit out of town and there wasn’t much in the way of hostel camaraderie during our stay. We were tickled by the local luggage service, however, which consisted of a bicep-flexer tossing our bags into a custom push cart and leading the way to our hostel for $4 each.

How to fill one’s days on such a charming island? Options are a-plenty. We’d originally enthusiastically planned to go diving though were warned off by the local dive shop due to the storm that had plagued us in Paraty and churned the visibility up to nothing.

Other tours for snorkeling, island hopping, and waterfall rappelling were appealing, however in the end we decided to give our budget a rest and entertain ourselves on the cheap. We spent the majority of our time on Ilha Grande tackling three of the island’s sixteen signposted hiking trails — leading to just a few of its hundred and two beaches!

And, needless to say, with a professional shutterbug as my co-pilot (she took both the beautiful photos above!), photography walks were a fun part of almost every day. I love how creatively challenged I can be by my travels with Heather, and comparing the different ways we see the world through our lenses.

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Also kind of needless to say when it comes to the two of us, eating and drinking were also a main form of entertainment.

While Ilha Grande doesn’t have close to the dining scene that Paraty boasted, we did find a few favorites. was the perfect comfort food for our first chilly night, was a healthy dinner option, and was our pick for chic beachside eats in the sun — don’t forget to look for their special evening BBQ a few night a week, too! We both gave a thumbs up to the vegetarian-friendly self-serve buffet at , and the flavored mojitos and fresh empanadas at were definitely the hippest thing happening in town. And let’s just say we made a thorough sampling of the local açaí bowl offerings, and we weren’t let down once.

On our final morning, we decided to go wild and fork over a few riels for fun. While rentals for bikes, surfboards and kayaks were tempting, we saved our mild splurge for a mutual favorite: stand up paddle boarding.

For 40BR each (about $11), we had an hour to play in the bay. We were heading onward to Rio de Janeiro that afternoon, and while it was a city I’d looked forward to visiting for much of my life, I couldn’t help but feel wistful about leaving Ilha Grande. The three nights we’d originally budgeted due to rumors of horrific wifi (a serious concern for two online business owners) suddenly seemed far too short. We’d actually tried to extend our trip by another day, but found our transfer was non-refundable and couldn’t be budged.

We were both overwhelmed with happiness as we paddled around and looked back on the beautiful island we were saying goodbye to all too soon. How rare to find such a gem of nature, so unsullied by overdevelopment. Ilha Grande is truly a special place.

Ilha Grande left a big impression on my heart. Here’s hoping I’ll be back someday!

This looks so amazing, truly a gem in a world of over development! It reminds me a bit of Caye Caulker, Belize (I spent spring break last year there thanks to your posts about it, I absolutely loved it) except slightly less developed. Looking forward to hearing about those hikes.Cate recently posted..

Brazil was definitely the most expensive place I’ve been thus far in Latin America… I can see why so many backpackers leave it off their itineraries out of budgetary concerns! And this was at the height of Brazil’s financial crisis! Part of the reason I waited so long to go was just to have the financial means to do so.

Ha, I had a feeling I’d get this reaction, posting at this time of year! But really it all comes down to dressing correctly for the weather, and coming straight from Thailand and Indonesia we were just simply not packed for high winds and temperatures in the 50’s. If I hadn’t panicked and bought a pair of jeans in Koh Samui right before leaving, I don’t know how I would have managed! Most of the Brazilians we saw in Paraty were bundled in puffy jackets and hats and scarves, and we had jeans and hoodies. We were so laughably unprepared.

What a lovely place! I know so little of Brazil that I’ve never heard of Ilha Grande, so thank you for sharing the stories! It’s terrible when you go travelling unprepared for the cold – I’m all too used to having to wear all my clothes because I thought if it’s warm during the day it has to be warm at night to!Dominique recently posted..

Yeah, we really didn’t do our research correctly! I definitely looked at the daytime temperatures and kind of gauged my packing on that, but I had fairly limited options considering I was coming from Thailand anyway. But I didn’t account for the drastic change between day and night! It was wild!

Actually, not as bad as we’d imagined! Not quite good enough for proper Skype calls or streaming, but we were certainly able to answer emails and upload Instagrams and do all the essentials for a few days. We definitely could have stayed another night or two without too much hassle, business-wise.

Sounds like three days is around the average! I thought it was the perfect amount of time for a first glance at the island, but four or five would have been ideal if we’d added in some diving or even a bit more hiking.

Nice pictures of Ilha Grande! I have a friend who already went to this paradise a lot of times. I wish to visit someday (and it´s a shame because I live just 5 hours by car!) As a brazilian, the prices for beach vacations or other cities are really expensive lately…If Brazil is expensive for foreigners, could you imagine for us (we are paid in R$, and not in US$) 🙂

I can indeed imagine, Erika! I was impressed by the number of Brazilians I met traveling around their own country. It’s not often that you meet domestic travelers in hostels and in Brazil, they made up the overwhelming majority. It was a very refreshing change!

What a beautiful island! Those mountains behind you in the paddleboard photos… swoon. Looks like a great place for daily morning hikes followed by afternoon swims and lots of food!Kate Storm recently posted..

Ok lady, I undertsand! I am a big fan of you, you don’t imagine how I love you! I have never been to the USA, but I speak exactly like you americans, your pictures are incredible, I love the way you explore the world, the posts are amazing as well! I want to talk to you more!

I'm a New York native who left my home to explore the world slowly and thoroughly. I’m just a little obsessed with photography, scuba diving, and reading guidebooks to countries I have no immediate plans to visit.